1. Field of the Invention
The present invention relates to compounds of the general formula I ##STR2## where X is unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, Y is chlorine, bromine, carbamyl or cyano, Z is hydrogen, carbamyl, cyano or acetyl, R is hydrogen or C.sub.1 -C.sub.3 -alkyl, R.sup.1 and R.sup.3 independently of one another are each hydrogen or unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl or aryl, R.sup.2 is hydrogen or unsubstituted or substituted alkyl and R.sup.1 and R.sup.2, together with the nitrogen atom, form a saturated 5-membered or 6-membered ring.
2. Description of the Preferred Embodiments
Examples of radicals X are C.sub.1 -C.sub.8 -alkyl which can be substituted by chlorine, bromine, cyano, hydroxyl, C.sub.1 -C.sub.4 -alkoxy, phenoxy, C.sub.1 -C.sub.8 -alkoxycarbonyl, unsubstituted or substituted phenyl, carbamyl or amino, and C.sub.5 -C.sub.7 -cycloalkyl, and phenyl which is unsubstituted or substituted by fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy.
Specific examples of radicals X are: ##STR3## where T is F, Cl, Br, CH.sub.3, OCH.sub.3 or OC.sub.2 H.sub.5.
Examples of radicals R.sup.1 and R.sup.3 are:
1. Unsubstituted or substituted alkyl, such as CH.sub.3, C.sub.2 H.sub.5, n-C.sub.3 H.sub.7, CH(CH.sub.3).sub.2, n-C.sub.4 H.sub.9, CH.sub.2 -CH(CH.sub.3).sub.2, ##STR4##
2. Unsubstituted or substituted cycloalkyl radicals: ##STR5##
3. Unsubstituted or substituted aralkyl radicals: ##STR6##
4. Unsubstituted or substituted phenyl radicals: C.sub.6 H.sub.5, C.sub.6 H.sub.4 CH.sub.3, C.sub.6 H.sub.3 (CH.sub.3).sub.2, C.sub.6 H.sub.4 OCH.sub.3, C.sub.6 H.sub.3 (OCH.sub.3).sub.2, C.sub.6 H.sub.4 Cl and C.sub.6 H.sub.2 (OCH.sub.3).sub.2 Cl;
5. The radicals CH.sub.2 CH.dbd.CH.sub.2, CH.sub.2 COOCH.sub.3, (CH.sub.2).sub.5 COOCH.sub.3, (CH.sub.2).sub.5 COOC.sub.2 H.sub.5, (CH.sub.2).sub.5 COOC.sub.4 H.sub.9, ##STR7## where n is 2, 3, 4 or 6.
6. Acyloxyradicals: (CH.sub.2).sub.2 OCHO, (CH.sub.2).sub.2 OCOCH.sub.3, (C.sub.2 H.sub.4 O).sub.2 CHO (C.sub.2 H.sub.4 O).sub.2 COCH.sub.3, (CH.sub.2).sub.2 OCOC.sub.3 H.sub.7, ##STR8## (CH.sub.2).sub.2 OCONHC.sub.6 H.sub.4 Cl and (CH.sub.2).sub.2 OCONHC.sub.6 H.sub.3 Cl.sub.2 and the corresponding radicals containing (CH.sub.2).sub.3, (CH.sub.2).sub.4 or (CH.sub.2).sub.6 instead of (CH.sub.2).sub.2.
7. Acyl radicals: CHO, CH.sub.3 CO, C.sub.2 H.sub.5 CO, C.sub.3 H.sub.7 CO, ##STR9## C.sub.2 H.sub.5 CO, CH.sub.3 C.sub.6 H.sub.4 CO, C.sub.6 H.sub.5 CH.sub.2 CO, C.sub.6 H.sub.5 OCH.sub.2 CO, CH.sub.3 SO.sub.2, C.sub.2 H.sub.5 SO.sub.2, C.sub.6 H.sub.5 SO.sub.2 and CH.sub.3 C.sub.6 H.sub.4 SO.sub.2.
Examples of preferred substituents are hydrogen, C.sub.2 H.sub.5, CH(CH.sub.3).sub.2, n-C.sub.4 H.sub.9, CH.sub.2 --CH(CH.sub.3).sub.2, ##STR10##
Examples of radicals R.sup.2, in addition to hydrogen, are ##STR11##
Examples of radicals formed by R.sup.1 and R.sup.2 together with the nitrogen atom are: ##STR12##
Depending on their structure, the compounds of the formula I are suitable, for example, as disperse dyes for synthetic polyesters, as transfer dyes for dyeing thermoplastic materials consisting of, for example, polystyrene, polyethylene, polypropylene, nylon or their block polymers, and for dyeing cotton and union fabrics of cotton and polyesters, for example by the method described in German Patent No. 1,811,796.
As a rule, very fast dyeings and prints are obtained.
The dyes are as a rule further distinguished by good color build-up substantially independent of the pH-value of the dyeing bath.
Particularly important compounds are those of the formula Ia ##STR13## where B is methyl or isopropyl, or is phenyl or benzyl which is unsubstituted or substituted by methyl, methoxy, chlorine or bromine, and R.sup.1 and R.sup.3 have the above meanings. R.sup.1 is preferably phenyl which is unsubstituted or substituted by methyl, methoxy, chlorine or bromine. Particularly preferred dyes of the formula Ia are those in which B and R.sup.1 are each phenyl which is unsubstituted or substituted by methyl, methoxy, chlorine or bromine, and R.sup.3 is one of the abovementioned radicals which is bonded to the amino group via a secondary carbon atom.
The compounds of the formula I can be prepared by reacting a diazonium compound of an amine of the formula ##STR14## with a coupling component of the formula ##STR15## by a conventional method.